Triethylamine → HCID 43196838, compound

HRID 1958509Notes

Reaction equation

HRID 1958509 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:20]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11])(=[O:23])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 43196838HCID 43196838, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of indoline-2-carboxilic acid (8.16 g, 50 mmol) and triethyl amine (10 mL, 71.74 mmol) in anhydrous CH2Cl2 (60 mL) containing catalytic amount of DMAP was added dropwise a solution of propionyl chloride (5.55 g, 60 mmol) in CH2Cl2 (20 mL) at 0° C. The reaction mixture was stirred at this temperature for 15 min and then at room temperature for 2.5 hours. The reaction mixture was washed successively with 5% aqueous KHSO4 solution (2×20 mL), brine (25 mL), dried over Na2SO4, and evaporated under reduced pressure to dryness. The residue was crystallized from methanol to yield 1-propionyl-2,3-dihydro-1H-indole-2-carboxylic acid as a white solid, 9.19 g (83%): mp 173-175° C.; 1H NMR (DMSO-d6) δ1.05 (3H, t, J=7.6 Hz, Me), 2.51 (2H, d, J=7.6 Hz, CH2), 3.17 (1H, d, J=16.0 Hz, CH), 3.57 (1H, dd, J=11.0 Hz, J=16.0 Hz, N—CH), 5.15 (1H, d, J=16.0 Hz, CH), 6.98-7.01 (1H, m, ArH), 7.15-7.23 (2H, m, 2×ArH), 8.07-8.09 (1H, m, ArH), 13.26 (1H, brs, exchangeable, OH). Anal. Calcd. for C12H13NO3: C, 65.74; H, 5.98; N, 6.39. Found: C, 65.73; H, 6.07; N, 6.34.

Workup

  1. waitat room temperature for 2.5 hours
  2. washThe reaction mixture was washed successively with 5% aqueous KHSO4 solution (2×20 mL), brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure to dryness
  5. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-563343a1462c42e4908b09663721942d
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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